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Italy: Plan your own vs Travel Agent

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This is my first time visiting Europe and I'm planning a trip to Italy end of this month (October) with my wife and 3 kids (aged 6,4,2).

My draft itinerary as follows:
1st day (Thu): Arrive Rome afternoon (Free and easy)
2nd day (Fri): Colloseum Walking Tour and other places on the 101 Tourist bus
3rd day (Sat): Travel to Florence; Visit Uzzi (4 hours walking tour)
4th day (Sun): Day trip to Pisa.
5th Day (Mon): Travel to Venice, free and easy
6th Day (Tue): Venice (3 hours walking tour)
7th Day (Wed): Travel to Milan (Free and Easy maybe visit Duomo)
8th Day (Thu): Day trip to Lake Como
9th Day (Fri): Free and easy and depart from Milan

I've got a quote from a travel agent for the above itinerary which plan and book every single thing of my trip for of course slightly more (around USD 6,000) which includes 3* accommodation, meet and greet, train tickets, transportation to and from hotel, guided walking tour at each city and a car with driver to Lake Como.

I was thinking that maybe i could save some money by planning the trip on my own but i'm not sure if i can plan it smoothly and need advice/tips/hints on the following.

1) Any tips on how to book the train tickets. Are they really strict on the timing? How do i book for a family so that we can seat together? Do i get a ticket or just use the print-out to board the trains?

2) On accommodation, i don't know if finding one which is near to the train station is suitable. I've read mixed reviews concerning the safety of the hotels near train stations.

3) Is hotel booking via Booking.com secure/honoured by the hotels in Italy. I've been to countries where i have to personally call again the hotels to re-confirm my booking.

4) Is taking the Rome 110 Tourist bus ticket worth it? Or is Rome small enough to walk through to all the places of interest.

5) How will the weather normally be at this time of the year? Should i bring a jacket? Rain coats?

6) Any other ideas to add to my itinerary? Fillers for the free and easy session perhaps?

Appreciate any advice from those experienced travellers out there....

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